Big Changes

I’ve neglected to mention that I’m in the midst of a career change.  I’d spent a long time building up my landscaping business and 2018 was a record year, but I was getting tired of the grind and ready to try something different.  So I was lying in bed one Saturday morning back in April scrolling through help wanted ads on Craigslist, and there on the second page was my dream job working on a farm with chickens and ducks – the latter of which are my favorite animals.  They were having open interviews all weekend, so I was at the farm three hours later and started work on Monday.

It was as easy as that.  Everything for me is as easy as that… except dating, for some reason.  But if that’s the trade-off I’ll take it.  Craigslist has been a boon to my life, though.  I’ve made thousands of dollars selling off old possessions.  I’ve picked up loads of stuff and paid it forward by giving away tons of stuff as well.  And now I have a new part-time job.  I’m still working my old job, but between the two I’ve brought in an extra 10-15K this year.  Not bad.  The plan for next year is to sell off my business and work full-time at the farm.

Holy shit – and talking about how lucky I am?  I literally just got word as I’m typing this that I won my marching band’s Super Bowl raffle.  They drew the winning ticket at the holiday party (I didn’t go) so they just texted me about it.  It was a trip for two package including airfare and a three-night stay in a hotel.  Well, I don’t give a flying fuck about football or any professional sports, so I opted for the cash payout instead (of a considerable amount).  Now the band is going to sell off the Super Bowl package to someone else and likely turn a handsome profit, so everybody is making out great with this deal.

Not only that, but I entered a celebrity death pool this year.  You pick the names of 20 celebrities you think will die in 2019, and if enough of them die then you win.  The rules are a bit more complex than that, but in any case we’re ten days out from the New Year and I’m 40 points ahead of the next person.  So I’m likely looking at another handsome payday if nobody else’s famous picks croak before then.

In the meantime, I’ve just celebrated my 35th birthday.  I guess it’s something of a milestone.  I certainly look and feel the best I’ve ever been.  What hitting 35 means for my dating prospects remain to be seen.  I deleted Bumble again after my last date with Virgin Girl.  Maybe I’ll pick it up again after the holidays, but I’m not excited at the prospect of returning to online dating.  Until I’m enjoying life and wishing everyone a very happy holiday season.

The Virgin Mary

I gave it a month after my breakup before I re-downloaded Bumble.  I noticed a couple of changes.  First, they no longer show when someone’s read your message.  Second, they have swiping limits now.  I hit them during my first few days on the app, but haven’t since.  Anyway, I picked up a bunch of matches, albeit at a slightly slower pace than during my last few stints on Bumble.


I thought I hit paydirt with this one.  31, Lived only a few miles away, didn’t want kids, cute as hell, and the conversation was fire.  She was willing to meet sooner rather than later, so we set a date at a craft brewery the following night.  Things seemed off from the get-go.  As soon as I showed up she was low-energy and a bit meh.  I did my best but things didn’t flow like they did online.  This has happened to me quite a few times and it’s frustrating as hell.  It’s even more frustrating when you feel like the only one making an effort.  I’ve literally made up index cards of questions and topics in the past and studied them beforehand in case things lagged.  I didn’t do that this time but – social media ninja that I am – I’d found her on Facebook and combed through her interests.  Even working some of those into the conversation didn’t breathe more life into the proceedings.  The last straw was when she picked up her phone for the tenth time and it looked like she was messaging someone on Bumble.  Okay.  I downed the rest of my drink and told her good night.


This one definitely went better than the last.  29, also lived a few miles away, also didn’t want kids (woohoo!), but her pictures were a tiny bit suspect.  We met at a bar, and I warmed up to her over the course of the evening.  For once the in-person banter matched the online banter. We traded stories back and forth, compared dating experiences, talked about our crazy families.  We sat at the bar stools with our legs touching, and I was going to go in for the kiss afterwards but I got the cheek instead.  Oof.  Okay.   The next day I texted her to reiterate what a nice time I had, and she concurred.  I dithered about, wondering if I should ask for a second date.  In the end I took my indecision as a sign and just left it at that.


Finally!  A great first date and an even better second date.  The two best dates I’ve had in a long, long time.  Unfortunately there won’t be a third…

She was 28, lived a little further away, cute as hell, but unfortunately wanted kids.  That came up pretty early in our online conversation, and I warned her that I didn’t and that wasn’t going to change.  So if that wasn’t going to work for her, I’d understand.  Nevertheless she persisted, but I knew this was going to have a short shelf life.  That’s okay, though – I’m open to short-term dating.

Our first date was at a board game cafe, which worked out perfectly because she loves board games and hosts regular game nights.  We were there for three and a half hours.  Afterwards we waited outside for her Uber and I put my arms around her to keep her warm.  “You know, we have time for one more thing…” I said.

“What’s that?” she asked, grinning up at me.  I leaned down to kiss her in response.  It was a bit awkward with the height difference, but it was still really nice.  We made out in the shelter of a doorway for a minute until her ride pulled up, and I skipped across the intersection as she pulled away.  Now that was more like it!  Finally, a great first date.  There was definitely going to be a second.  It was a week and a half before she had another free night, during which the anticipation was killing me.

This time we went to an Italian restaurant, putting away the food and wine for three hours.  Instead of calling another Uber, I offered to drive her home and she accepted.  Five minutes in and she brought up the whole not-having-kids issue again.  “I hate to be a debbie downer…” she began.  She’s looking to get married and have kids as soon as possible, and if I was dead-set on no kids… but she really liked me and was confused as to what do.  Maybe we could just date casually?  I said I was open to that, yet she was still uncertain.

By this time we were back at her house.  I pulled into the driveway and we sat there continuing our discussion.  She was all in a dither about things.  We interrupted our chat for another makeout sesh.  This one was pretty hot and heavy.  She tilted her seat back and pulled me over to her side so I could get on top of her.  I lost track of the time but we must have been at it for a half-hour.  She even let me feel her up and – after I confided being driven crazy by her low-cut shirt on our first date – she hiked her sweater up so I could pull her tits out of her bra for a better look.  They were awesome.

Then she dropped another bomb.  She was a virgin.  Well, I can relate to being a virgin at 29.  I even like the idea of being someone’s first.  But she told me she was a “good Catholic girl” and saving herself for marriage.   OMGWHAT?  So if we were to date casually, there wouldn’t even be sex.  Wtf would we be doing then?  I knew she was politically conservative (itself a potential issue down the road), but to be sexually conservative as well?   Yeah, this wasn’t going to work at all.  So long story short we parted ways.  Sucks because we got on so well and really liked each other.

So that’s the latest.  If nothing else I got some kissing and titty action. Now if I could just find someone like her who’s also a huge slut…

Just wondering – should I bring back the date counter?  What do y’all think?

So… I Had a Girlfriend

It’s been a while.  The last time I was here, I had a handful of Hinge matches that weren’t really doing anything for me.  I decided to junk the app.  However, one of the girls I was talking to noticed I was gone and panicked.  She messaged me on Instagram (slid into my DMs, as the kids say) and was suddenly a lot more conversational.  Well, this was more like it!  We went on our first date a few days later.


Dawn, 28, a teacher and a local!  She lived only a few miles away, and coincidentally on a road I frequently traverse.  We met a local pub halfway between our houses.  I normally detest meeting in bars and such, but it was a Monday and mercifully quiet.  We got on pretty well, and as I walked her to her car afterwards I saw it was conveniently parked right next to mine.  I took that as a good sign.

We stood there for a moment looking at each other before she giggled and said, “I always get awkward at this part, I never know what to do!”

“I do,” I said and I took her in my arms and kissed her.  We made out for several minutes, ignoring the soft light rain that had developed.  She told me I was good kisser, and she wasn’t afraid to use her teeth and bite my lips a little.  Ooh, a biter!  Does that mean she liked it rough?  The thought got me super hard.  There was definitely going to be a second date.

We went to a mac and cheese place for our second date, and across the street for brews and board games afterwards.  However it was chilly inside and rainy and damp outside – much like our first date – so I suggested going back to my place where it was warmer.  I worried she might take it the wrong way and question my intentions.  Fortunately she was down for it, and we watched a movie and had a makeout session afterwards.  But we didn’t go further than second base.  It was only the second date and she didn’t want to rush things.

Third date was lunch and a hike, fourth date was dinner, and fifth date was dinner at my place.  I’d always wanted to cook dinner for someone and I finally got  my chance.  I thought she might stay the night but she left at 11:30.  Before she left there was some making out, some clothes came off, and my dick went into her mouth.  I couldn’t cum though.  I very nearly did, but I got some weird mental block and just couldn’t bring myself to do it.  What the hell.  And still no sex because now she was on her period.  Didn’t bother me but apparently some women are icky about that sort of thing.

Sixth date was pizza and board games, again at my place. She brought her Chrome firestick and we watched the Zac Efron Ted Bundy movie on Netflix. It was very good. Afterwards we cuddled and kissed a little bit, but I held back because I didn’t want to get too worked up and develop blue balls. She was still spotting from her epically long period (her gyno said it was due to her switching birth control pills), but eventually I said “fuck it” and starting making out with her for real.

Eventually she kissed her way down and gave me a blowjob. This time I came in her mouth, and she swallowed.   Holy fucking shit.  It felt amazing and took me a while to recover from that.  She was the second girl to ever go down on me and the first to go all the way with it.  Definitely worth the 34-year wait.  This girl was definitely a keeper. Even better, I awoke to the good news that her period seemed to be over!  Did I want to try having sex?  Pfft.  You don’t have to ask  me twice.  I grabbed a condom and when it was over I had filled that thing to near bursting.  Phew.

Over the next few months we had some great sex.  I lost count of the number of times we did it, but it was certainly in the dozens.  She had the most voracious appetite of anyone yet. One night she came over to my place wearing nothing but a trenchcoat over some sexy lingerie.  That was one of my hottest encounters ever.  We even experimented with paddles, handcuffs and blindfolds – more bucket list items for me.  There was good orgasm equality and we often climaxed simultaneously or close to it.  I scored some more blowjobs and happily returned the favor.  Dawn was only the second chick to ever let me go down on her, so it was nice to get some more practice.

Dawn helped me cross a lot of firsts off my list.  I finally had someone to introduce to family and friends.  I went on my first ever double date.  I updated my Facebook to “in a relationship.”  She joined me in the gym and we worked out together.  We watched a fireworks display.  I posted my first ever #wcw.  And then just regular couples stuff I’ve long relished the chance to do.  It was so nice to have someone to talk and text with all the time, sharing every weird or random thought.  Sometimes I’d wake up and just watch her sleeping next to me, scarcely daring to believe my luck.

So what happened?  Everything was going great as we approached the five-month mark, until I got the dreaded “we have to talk.”  Turns out… she did want kids after all. In the beginning she said she didn’t want kids, but ended up changing her mind.  I was afraid that was going to happen.  She was a Pre-K teacher, and anyone who teaches kids likes kids, and anyone who likes kids usually wants kids.  And if they want kids, then they have no future with me.  Dawn was looking towards the future, so that put the kibosh on things.  At least that was the reason she gave. I have no reason not to believe her, so I’ll accept that.

In the end I was dumped but at least we parted ways amicably and I have nothing but happy memories.  I gave the relationship everything I had.  Nothing was left undone or unsaid and I have no regrets.  Disappointing to say the least, when she checked off so many boxes for me. And five months – that’s a new record for me. 

All the girls I’ve had success with were fellow Sagittarius.  I don’t put much stock in that sort of thing, but it’s funny how it’s happened that way.  We certainly had a lot in common. Dawn was a brunette, which is also in keeping with the pattern…even if she did go blonde for the summer.  They’ve also been trending younger: 39, 37, then 34, and now 28.  Younger seems to be better in my experience.  More fun and spontaneity, less baggage, and greater sexual energy and openness.

While I’m sad that my time with Dawn has come to an end, I’m also kind of excited to see what’s next.  But I don’t know if I could go back to online dating.  (Of course, I keep saying that…) Even with that as a tool, it takes an average of 1-2 years to find someone interested in me in return, expending a great deal of time and energy in the process.  We’ll see.


Well that didn’t last long.  I was feeling certain urges, and since I’d heard talk of it I figured I’d try Hinge.  I’m only a few days in and so far I’m not a fan.  As the tagline says, there’s no swiping here.   You fill in your stats, post a half-dozen pictures, and choose three questions to answer.  The questions are things like: “Worst fad I ever participated in,” “A fact people are surprised to learn about me,” “My ideal first date is” or “I’ll fall for you if” etc.  When someone likes your picture or answer, you can then message with them.

Unfortunately there’s no About Me and most people’s answers are generic and uninspiring.  So while I  come across many I find attractive, ultimately I have nothing to say to them.  I need more to work with than basic pictures and “I like to have fun and laugh.”  I’m also seeing many of the same faces from Bumble.  Some of them I’ve even seen since I started online dating, which was several years ago.  At least I’m not the only unlucky one out there.

But if you dig long enough you find a couple of prospects.  I ended up with six, and I met one tonight.


She lived only a few miles away so I picked out a wine bar at a nice halfway point.  I had a seat at the corner of the bar and thumbed through the drink menu while I waited.  She walked in a few minutes after I arrived and she looked just like her pictures.  Nice.  After we got our drinks I led her to a table in the back where it was a little quieter and more private.

We talked for an hour and a half, but despite asking about her family, her job, her life goals, her gym routine, and whatever else I could think of… I can count on one hand the number of times she asked me anything at all about myself.  I even left a number of gaps in the conversation to give her an opportunity to do so.  Instead I had to keep volunteering information.  I realized this about halfway through, after which it started to annoy me.

Finally at 10 I announced that we should get going because they were closing (which they were).  We walked outside and she lingered there.  I wondered for a wild second whether she wanted me to kiss her, but I doubted that.  I hadn’t gotten any sense at all that she was interested in me.  So I just gave her a hug, said nice to meet you, and trotted off.  I said nothing about meeting again.  And that was that.

So.  Online dating.  Same shit, different day.  I still have five other prospects, but there’s only one other serious contender and that conversation is rather one-sided too.  No reason to expect things to be any different in person.  It’s just really hard to find someone I click with and where the banter is fire.  Like I said in a previous post, it’s 1 out of 100 matches. I’ll give Hinge another week, by which point I’ll likely delete that too.

In other news, if you haven’t seen my previous post I’m doing an Ask Me Anything.  If there’s anything you ever wondered about me, head over there and drop me line.  I may collect all the questions and answers into a future post.  And if you want to participate, please comment on that post instead of this one.  That way it’s easier for me to keep track of all the Q&As.





Too good to be true

Womp womp.  My three month vacation is over and I’m finally back to work.  No complaints, though.  As much as I enjoy my time off, I also miss stacking that paper.  I’ve got my eye on some more big-ticket items this year, and funds were getting light after a kitchen makeover, a new car and other purchases at the end of last year.

In other news, I’ve deleted Bumble yet again.  Let’s see how long this lasts.

There was one last girl in the queue and after a couple of failed attempts we finally set up a date a few weeks ago.  However, she developed cold feet the day of.  Sigh.  What is it this time?  Well, she felt bad I was traveling all the way to meet her.  Okay, why?  Well, she felt more pressure if I was traveling all that way just to meet her, and maybe we should meet when I was already in the area.  I still didn’t understand why she felt pressure, but I agreed to wait and talk on the phone in the meantime.

A few days of phone tag commenced, and when I finally caught her we chatted for a minute and a half before she said she had to go and could she call me back in a little bit?  Sure, I said.  And I never heard from her again.  Either it was something I said, she didn’t like the sound of my voice, or by that point she was as over things as I was. It’s hard enough trying to date someone who’s busy busy busy all the time, but to add travel time on top of that?  Not gonna work.

I feel so much better having jettisoned online dating apps again.  It’s such a roller coaster and I needed the break for my mental health.  And then something happened to perk me up and pique my interest.  Long story short, I’d made up a joke Instagram, and a girl with a similarly-themed Instagram found my account.  She lived locally.  What’s more, we were both in marching bands AND played the same instrument.  No way.

Then I found her regular IG.  Similar tastes in geekdom, music, and wacky sense of humor?  I couldn’t believe my luck.  Was this really happening?  A couple weekends ago our bands were in the same parade and lined up on the same street as well.   She came running over to me.  “Are you Tommy?” she asked excitedly.  Indeed I was.  We chatted for a couple of minutes before we had to rejoin our respective groups.  She was cute – even better looking than her pictures.

A few days later I saw a music performance at the local theater.  A lot of people from my and other marching bands were there, and I wondered if she was there too.  Turns out she was!  Afterwards I was in the lobby with a group of friends, and suddenly she popped up in front of us.  She said hello to everyone.  And then… she introduced us to her boyfriend Chuck.  Seriously??  Ugh.  I knew it was too good to be true.  I was surprised because she posted a lot on social media, yet there wasn’t a single picture or mention of this dude.

So that takes care of that.  Single with no prospects for the foreseeable future.  I’ll be ringing in the big 3-5 this year.   Recently I overheard someone say, “if you’re 35 and still single, you’re probably a loser.”  Well I don’t agree with that. I don’t think I’m a loser – even if I did have better luck in high school.  Somehow I had more girlfriends when I was thin, bespectacled, pimpled, socially hapless and poorly-dressed, as opposed to today when I have so much going for me.  A bit funny, isn’t it?

Deep down I still would really like to find someone.  But it’s a want, not a need.  And as I’ve said before – my life is amazing in every other aspect, so if being alone is the trade-off I’ll happily take it.

We’ll see what happens, though.

The Last Girlfriend (Part 2)

Continuing from my last post, this is the story of my (so far) one and only long-term relationship.  This happened when I was 17-18.  


When I got to Patti’s house I stopped on the sidewalk outside. The light was on in the living room and I knew she was on the computer as always. Her mother’s car was gone from the driveway; she was working late again. I paced outside for a bit, screwing up my courage and rehearsing what I would say. When I was ready, I ran up to the front door and knocked. As soon as I did I forgot all my lines. She opened the door, surprised to see me there at such a late hour and with a trace of concern on her face.

“Hey – what’s up?”

“Uh…can we talk?” As soon as I said that a flicker passed over her face. She must have known what was coming.

She came out and we sat on the front steps, since I wasn’t allowed inside when her mother wasn’t home. In a few minutes it won’t be an issue anymore, I thought.  The night air was crisp and cold since it was only the middle of March. After a few awkwardly silent moments, I cleared my throat.

“I don’t think this is going to work out,” I said.  She looked down at the ground and nodded. I knew she was thinking along the same lines, and mostly for the same reasons, even though she didn’t say anything.  I was going to miss that – the fact that our minds were so much on the same plane that we usually knew what the other was thinking.

But while we were so alike, we were also very different. And we were on different paths in life. We were going away to school in different states. And even if I had a strong enough desire to continue the relationship, I couldn’t have. Some people can have long-distance relationships. I can’t. I need that person here in my life, not hundreds of miles away, only to be seen for a few weeks during the year, without physical contact for long periods of time in between.

Not that there was much physical contact to begin with.  We were both virgins and progress was frustratingly incremental.  It was two months before she stopped freaking if I put my hand on her neck while we made out.  The first time I did that she pulled away and curled into a ball and started shaking.  Um, what?  I poked her and asked what was wrong.  “Usually when a guy does that, it means he wants something more.”

She finally confessed that she was making out with her ex boyfriend once and he touched her breast.  I waited, but apparently that was the whole story.  It took her a while to recover.

Three months in she was okay with ass grabbing.  Four months in – and this was a big day for me – she finally allowed me to touch her breasts.  Through her shirt.  It was a few weeks after I’d turned 18.

After eight months of dating she graduated to groping me in return – but only through my pants.  She dabbled with slipping her fingertips under the waistband of my jeans but wouldn’t go further than that.  Her reason?  “Well, if you came while I was touching you and it got on my hands, and then I touched myself down there and there was liquid seeping out of me, there’s a very small chance I could get pregnant.”

After a whole year of dating she felt comfortable enough to put her hand all the way down inside my pants – sometimes even pulling my penis out to squeeze it or run her fingers along it.  Only for brief moments, though.  Every time we fooled around she’d get me all hot and bothered, and then she’d pull away and we’d have to stop because she was afraid of going too far.

Whenever Patti was at my house I’d have to coax her over the threshold like a nervous stray cat.  She was scared that my neighbors would see her going inside and tell my dad who would in turn tell her mom.  *eye roll*  This wasn’t 1955.  This was 2002.  Not only did we not talk to our neighbors, we avoided eye contact if we went to the mailbox at the same time.  They didn’t give a fuck if I had a girl over.

Her fears weren’t without merit, though.  One day Dad came home early and nearly caught us fooling around.  We took shelter in a closet until the coast was clear. Dad had ladled out enough Catholic guilt over the years and I didn’t need any more helpings.  And Patti was a nervous wreck when we were at her house.  Every 30-60 seconds she’d race to the window in a panic thinking her mother’s car was pulling into the driveway.

However, one day we started getting really hot and heavy.  Shirts came off.  Her bra came off.  Then she took me by the hand and led me downstairs to the bed in the basement.  Holy shit, after a year and a half this was finally it!  We lay down on the bed and continued making out, but after a minute I saw the familiar look in her eyes.  She was getting spooked again.  Sigh.  So I suggested she gave me a hand job.  Or a blow job.

Soon I began wishing I hadn’t.  She didn’t seem to have any clue what she was doing. She moved my dick around like it was a joystick (I know… it is).  She rubbed it between her hands like a Boy Scout trying to start a fire with a stick.  She blew on it.  No, she didn’t blow me.  I mean she literally blew air at it.  Then she squeezed it so tightly that the head turned purple and I was waiting for it to explode and confetti fly everywhere.

This went on for about ten or fifteen minutes. Finally I couldn’t take it anymore.

“All right, stop.”

She let go of me.  Phew.  “What’s wrong?”

“That’s not how you jerk a guy off,” I said, trying to hide my exasperation.

“Show me, then,” she said, sitting back on her heels and folding her hands in her lap.

So I did. I sat up on the bed, jerking off in front of her with my tighty-whiteys around my knees.  And she just sat there looking at me.  The whole time I just kept thinking to myself:  this sucks… this really sucks… I could be doing this at home…

“Okay,” she interrupted. “Let me do it now.”  And she took my dick in her hands and started over.

Five minutes later she was still at it. “Nothing’s happening,” I said pointedly.

“Well, it’s getting really hot…” she observed. Yeah, because it’s getting really pissed off, I thought.  I wrapped her hands around my dick with my hands and moved them up and down to give her the idea.  She still wasn’t quite getting it, and it definitely wasn’t doing anything for me.  Finally I’d had enough.  I pulled my clothes back on and said I had to go.  Then I went home and finished myself off.

I thought about what to do next.  Over time the spark had faded between us and it felt like we were just going through the motions.  Our late night chats were rare and conversation was dwindling.  All we had left was fooling around, but it was proving to be frustrating and unsatisfying.  So three days after President Bush started dropping bombs on Iraq, I walked back over to Patti’s house and dropped a bomb on her too.

She took it well at first, and then broke down in tears.  And that was that.  She moved on to date (and have sex with) other guys. Then she later dropped a bomb of her own:

She was gay.

Except… she still liked guys.

So she was a gay man trapped in a girl’s body.  She eventually moved to Canada, had all her equipment changed over, and began her new life as Paddy, aka The Boy Formerly Known as Patti.  And that’s the last I ever saw or heard of her.

After I dumped her, I started feeling ashamed of myself.  Did I really break up with her because I couldn’t get sex from her?  What a horrible thing to do.  I remembered how I always had to initiate fooling around or making out.  Nearly every single time.  While she would reciprocate and get into it, she almost never made the first move.  I started feeling like a monster as I reflected upon that fact.

For a couple of years I felt like I didn’t deserve to be with another girl, lest I treat her like a piece of meat too.  I spent half of my 20s looking for someone, and the other half not looking and not caring if I ever did.  But I didn’t go on another date for at least ten years.  I was year into this blog when I finally dated again.  30 was looming uncomfortably large on the horizon.  I didn’t want to be a 30-year-old virgin, but 31 proved to be the magic number.  Perhaps blogging is what helped me succeed.

Anyway, now you have the whole story.